“I decided that at least temporarily, something had to give.”

Image of Jill Berkowitz
From Teaching to Content

Jill Berkowitz loved parts of her work, but the impact it was having on her homelife had reached breaking point. Through assessing how she could use her skills in a different way, she's found a new path she adores – and one that allows her more time with her family. This is her story.

What work were you doing previously?

I had a career as a Middle School ELA (English Language Arts) teacher for a little less than 15 years.  

Prior to that, I worked in the editorial department of Pearson Education, a publishing company.

What are you doing now?

I’m now creating content (mostly written) for Clerk Chat, an innovative tech startup. 

I get to write daily and collaborate with an awesome team. 

Why did you change?

I'd always promised myself that when I felt it was time for a change, I'd step away from the classroom. 

15 years in and education had changed since I started teaching,  but so did my priorities and passions. So I decided to take time to reevaluate. 

I resigned at the end of the school year, and gave myself a few years to focus on family.  

When was the moment you decided to make the change?

As a teacher I had a lot of marking and grading to do. A LOT. 

I gave it my all, every time. And I saw significant results in my students’ writing, over time, so it was all worth it. 

But was it worth sacrificing my time with my family?  Definitely not. 

One weekend I found myself in a miserable puddle, trying to sift through tonnes of essays, when all I wanted to do was spend the day with my family. I chose the essays over the kids, and I regretted that every day after. 

I didn’t want to experience that feeling again. I decided that at least temporarily, something had to give. And within a week, I handed in my letter of resignation.

A huge takeaway from that moment was, 'What we see as a breaking point can actually be an opportunity for growth and change.'

Are you happy with the change?


Personally, I get the opportunity to try new things. For instance, I launched Clerk’s newsletter, and that’s been a really fun task! I’m often stepping out of my comfort zone, and finding my strengths. 

I don’t know if this is the case with all startups, but at Clerk there is an entrepreneurial spirit that you can’t find everywhere. I’m so proud of their drive and determination. I love watching the evolution of the products they’ve built and are building. 

What do you miss and what don't you miss?

I do miss the school where I was a teacher. 

I was there for so long that my colleagues (and the families) were around when I got engaged, married, and later when I had three children. We supported each other. 

That being said, I now get to work from home and I’ve found a better balance (or blend) between work and family. I’m happy to have given up the endless piles of papers to grade. While writing a blog post could, at times, take the same amount of time, it feels totally different. 

How did you go about making the shift?

I’m very proud of my skill set and felt I had so much more to offer than what meets the eye.  

When I considered my common thread through all my professional experiences, everything always led back to writing. 

A friend suggested I look into Upwork, essentially a work marketplace.  Although I was a freelance writer and editor in the past, Upwork was very new to me. 

I sent out lots of proposals and landed many “no’s” before I found my “yes.” And to be clear, the “yes” goes both ways. Clerk was my “yes.”

How did you develop (or transfer) the skills you needed for your new role?

Luckily this wasn't a challenge. 

I was hired for writing and that’s a strength of mine. I did, however, have to learn some tech jargon and acronyms. 

I researched or asked questions in meetings. I learned by doing. I joined some demos, too. We also have a weekly marketing meeting which gives me an opportunity to talk about what I’ve learned, ask questions, or share screens for anything that might still be confusing. 

I’ve learned so much about the telecommunications industry, because Clerk enables secure messaging (for instance SMS, WhatsApp, and 2FA codes) directly within Slack and Microsoft Teams. 

What was the most difficult thing about changing?  

When I found a way to start working again, my only real concern was, “Will I be able to stick with this and see it through?” 

Another thought is that, as a teacher I was tenured and very well established. When you switch careers, in a way you feel like you’re losing all that. 

So I had to change my mindset and really look at the situation as an open door to something new. 

What resources would you recommend to others?

I know a common rule of thumb is to leave a job knowing your next step. 

I happened to do it differently, because I resigned with the intention of taking time off to process. However, checking out options like Upwork may help you find opportunities that you can take on in-tandem with a full time job or as a standalone on the side while you figure things out. 

Also, there are so many online resources like HubSpot Academy, for instance, where you can gain knowledge and skills that you might not have had in a previous career. 

And, of course, LinkedIn. I’ve connected with so many people, from all over the world, and I’ve learned so much. If you find the right people, in the right niche, it’s almost like [insert class name here] 101. 

What have you learnt in the process?

I learned that I made the right choice. 

I knew that at the time, but immediately after, it felt so permanent which was a little scary. I wondered if I'd go back to teaching. I wondered if I gave up too much. I wondered where I'd be a year, two years, three years ahead. 

But here I am now and I’m very, very happy. I get to write every day, and whether it’s for Clerk, myself, or some other future client or company, I’ll know I did the right thing in chasing a dream and taking a leap. 

What would you advise others to do in the same situation?

Trust your instincts. 

They’re there for a reason. Sometimes, we need to step back and evaluate what's really important to us. It's okay to make a change, even if it's scary or seems unconventional. 

Thanks to our friends at Clerk Chat for this story.

What lessons could you take from Jill's story to use in your own career change? Let us know in the comments below.

Plus, if you know someone who's made a successful shift into work they love, we'd love to hear from you. Drop us a line at [email protected]. and you could win a £25 / $35 voucher in our monthly draw.